26 Best Restaurants in The Eastern Shore, Maryland

Surrounded by shops, lodging, and other eateries so very American, sophisticated Scossa almost seems out of place. From its sidewalk patio with wall-mounted fountains to its superb menus, Scossa Café is unmistakably northern Italian. The well-trained co-owners create lunch and dinner dishes with an Italian influence that does not overwhelm the fine ingredients. Samples of daily specials include braised lamp shank with artichokes, short ribs with Borolo wine sauce, roast rabbit campagnola, and soft-shell crabs alla provinciale. Brunch is available on weekends. Jackets are not required, but the cosmopolitan style of Scossa definitely attracts a well-dressed clientele who reserve ahead.

The spacious contemporary dining room, its porchlike extension, and an adjacent bar all face southward to the Eastern Bay and across this restaurant's slim namesake waterway separating Kent Island from the Eastern Shore mainland. One of the region's largest commercial fishing fleets is harbored next door. Specialties include a Caesar salad with fried oysters and grilled peppered tuna, served over sautéed spinach; and Crab Imperial, lump crabmeat, and select oysters baked with imperial sauce, topped with bacon. The Narrows' dinner menus include "Light Suppers," that encourage a second look at the to-die-for—or -from—desserts listing. checked aug 2010

Unobtrusively situated on St. Michaels' busy main street, 208 Talbot, long a favorite among discriminating diners, has several intimate dining rooms with exposed brick walls and brick floors. Specialties include such original first-course dishes as house-cured gravlax served with fresh mango, avocado, jalapeño pesto, and grilled flat bread; and more-traditional second-course entrées such as whole grilled rockfish accompanied by braised greens, grape tomato relish, and hush puppies; as well as a welcome variety of meat dishes. Small plates ($8–$14) are available for more conservative appetites, and on Saturday there's a four-course prix-fixe menu available ($55).

Consistently rated the top restaurant in Easton, The Bartlett Pear Inn Restaurant calls itself an "upscale Amerian Bistro." However, its roots are European and the menu features truffle butter paparadelle, braised snails, and paella. The decor and service are impeccable, as is the inn.

Young chef Ian Campbell, formerly of California's French Laundry, returned to his native Cambridge in 2007 to open Bistro Poplar. In the past few years it has been hailed as not only the best restaurant in town but one of the best on the East Coast. Campbell specializes in well-prepared, simple French food. Gourmands rave about his steak frites. The menu changes seasonally so no chance of either the chef or his followers getting bored. A definite must if you travel to this area.

This relaxed, contemporary dining room has high, sloped ceilings and skylights. Among its crab offerings and pasta, as well as chops and steaks, the café's most sought-after entrée is baked rockfish, but don't overlook the oyster fritters, a signature dish. Weekend nights are busy, and the service here is genuine and attentive.

Owned and operated by the same family since 1965, this St. Michaels landmark started as a clam- and oyster-shucking house for watermen long before that. Diners at both indoor and outdoor tables have panoramic views over the harbor to the river beyond, but dockside tables are the best. As the name suggests, this is the down-home place for fresh steamed and seasoned blue crabs. But the extensive menu also includes sandwiches and other light fare as well as other seafood and meat dishes. Children's platters are available, too.

This fine-dining restaurant, adjacent to and operated by the same owners as the Lighthouse Club and the Edge hotels, gives you white-linen treatment and views of soothing wetlands and the Bay, and stunning sunsets through its large windows. In addition to ubiquitous fresh-catch seafood, Fager's is renowned for its prime rib. There's an outside deck for more informal dining and a raw bar with lighter fare. Tchaikovsky's 1812 Overture is played every evening, with the tumultuous finale timed to coincide with the setting of the sun.

When the children need a break from the standard boardwalk fare, take 'em to this incredibly family-friendly restaurant, where children are part of the action. Youngsters can play on an awesome pirate ship or on the soft beach with the Frisbee that comes with their meals. The food is as easygoing as the atmosphere, from a fried chicken and barbecued ribs combo to skewered surf and turf. There's also a slew of economical offerings "From the Dock" and "From the Farm," as well as an extensive menu for "L'il Skippers," like pizza and mac and cheese. At night, a bit of a rowdy (yet civilized) older bar crowd likes to congregate on the waterfront benches.

This unusual watering hole is a welcome breeze of creative cuisine. Appetizers are light and delicate, like seared foie gras and asparagus shrimp risotto. Equally innovative mains include homemade manchego cheese gnocchi, seared duck with sun-dried cherries, and a pistachio-encrusted rockfish. The second and third floors open up to outdoor seating and views of the Bay. The cosmic Star Bar is a hot spot for local celebs and those looking for creative cocktails in a dark hideaway—and it serves tapas until midnight.

A most unusual and exciting blend of Pacific Rim, California surf, and grandma's kitchen await adventurous taste buds in this intimate venue. A tanuki is akin to a Japanese leprechaun, and the creative flavors here play tricks on traditional dishes. Imagine a restaurant serving buttery sushi and sashimi, lamb lettuce wraps, thai mussels simmered in Woodpecker cider, and a classic Hawaiian pizza under one roof. Run, don't walk, to this place, and make sure to check out happy hour (4 pm–6 pm) at the U-shaped bar.

On the mainland side of Kent Narrows, this family-friendly institution serves fresh catch directly from local watermen, some of whom are Harris family members. Nautical decor prevails in the large dining room, including an intriguing collection of oyster cans from an adjacent abandoned oyster house. Views over the shallow, twisting northern end of the Narrows toward the Eastern Neck National Wildlife Refuge can be stunning. Cream-of-crab soup and back-fin crab cakes are among the best around—the cakes are spicy enough to promote plenty of beer drinking.

Perched near the eastern end of the Bay Bridge, the upper-level indoor dining area and the broad veranda of this restaurant provide panoramic views westward across the Bay and of the city of Annapolis beyond. Sunsets can rival those off Key West, home of the restaurant's namesake. Entrées include Atlantic salmon and coconut sesame shrimp. In summer an informal bar and grill, Lola's, opens at 5 pm Thursday through Sunday on the lower level, with tables on the lawn adjacent to its private dock. Live music on weekends enhances its simple soup-and-sandwich menu.

This family-style restaurant is reason enough to stop in Grasonville. Watch for its sign off Route 50. Holly's specializes in all the Eastern Shore favorites, including a spectacular crab soup and crab cakes, but the fried chicken is the real attraction. Down-home and unpretentious, this is the real thing.

Kilby's Canal Creamery is the richest ice cream around. It is made from Kilby's herd of Holstein cows on a dairy located in nearby Rising Sun, which is why the motto is "from cow to cone in two days." Flavors include Holstein Cream, Cow Dough, and Chocotopia. Located in the historic district on the canal, it is open daily from 11:30 am to 9 pm.

A whimsical red, white, and green color scheme; painted vines climbing the walls; and polished wooden floors distinguish this bistro. Weather permitting, you can eat outdoors at wrought-iron tables in a brick courtyard. The creative and diverse menu changes twice a month, with such dishes offered as veal fettuccine Montrachet topped with goat cheese and a tomato cream sauce, and sauté of seafood including lobster, shrimp, and scallops.

A family-run landmark for more than 30 years, Mason's uses fresh ingredients from its own garden. The chef brings bold flavors like pan-seared crab cakes topped with a corn and soybean succotash, crispy-skin red snapper surrounded by braised artichokes, and gentle rockfish stuffed with lump crab meat, a local delicacy. Sip a classic martini in the swanky lounge while waiting for a table—make sure to ask for one on the porch in warm weather. Next door are a coffee bar and a food store that sells hard-to-find cheeses and meats, wonderful handcrafted chocolates, and all manner of esoteric edibles.

Feast on crab cakes, crab imperial, or stuffed and fried shrimp at the 1956 home of an O.C. institution that is the original of three Phillips locations here and has since grown into a regional chain (Phillips By the Sea 1301 Atlantic Ave.Phillips Seafood House 14101 Coastal Hwy.). Considered the city's most popular dining site, the restaurant has a dark-panel dining area with decorative stone floors, Tiffany-style hanging lamps, stained-glass windows, and funky wall art. Expect big crowds in the summer months. Its seafood buffet is served in an upstairs dining room.

This is the place to mingle with C'town residents as well as with Washington College students and local pols, for good conversation—indoors or alfresco—over fresh coffee (including excellent espresso) or fine wine, by the glass or bottle, to accompany hearty, healthy soups, salads, and sandwiches. Friday night is "wine night" with complimentary hors d'oeuvres, often accompanied by live music. Wi-Fi's in the air here.

Join regulars at this casual waterside restaurant and bar on the edge of town that has a wide-ranging menu with a Southwestern flavor. Mexican quesadillas are a Snappers specialty, but there is also an array of burritos, enchiladas, and fajitas. Jamaican jerk spices enhance burgers and crab cakes. From waters close to home, there's shrimp, stuffed or simply fried. Sandwiches, wraps, and pasta also satisfy the local lunch crowd.

One of the few restaurants in Chesapeake City, the Bayard House has cuisine and service that would stand out anywhere. Patrons in the know travel to this canal-shop eatery for dishes such as tournedos Baltimore, twin fillets of beef topped with crab and lobster; stuffed Anaheim pepper, chilies stuffed with lobster, crabmeat, and shrimp; and de rigueur Maryland crab cakes. The Maryland crab soup is even more widely renowned.

Housed inside a brilliantly converted theater, with its stage area is retained and periodically used for a variety of presentations, this eclectic eatery is well worth a meal, from vegetable risotto and jerk pork plate to, of course, crab cakes. Allow some extra time to wander the upper-level art gallery, its works all for sale. And you might luck into one of the periodic screenings of Runaway Bride. Sunday brunch and weekend dinners are popular with locals. On the weekends the stage has live entertainment.

Inside a former chicken barn about 15 mi from Salisbury, inverted bushel baskets now serve as light fixtures at this down-home crab house, where hammering mallets rival the beat of piano and banjo sing-alongs. The Red Roost gets rave reviews for its seafood specialties and ribs, as well as its meaty steamed crabs.

Don't let the name scare you: The namesake shark is meant to be your dinner, prepared any way you like. This off-the-beaten-path place in West Ocean City is worth the trek and takes advantage of every bay view, including from the sweeping rooftop bar. Dishes experiment with unusual flavors like the tuna with wasabi-cream sauce and pineapple meringue. Go for the Eggplant Tower stuffed with layers of shrimp, lump crab, and wild mushrooms with fresh-shaved Parmesan. Entrées are $5 from 3 pm to 5 pm, and a live jazz band plays on Thursday nights.

DPRICE This casual dockside restaurant looking southward toward the Chesapeake Bay Bridge in the distance has lots of local color. The menu includes ribs, steaks, and fried oysters, but its crab dishes are legendary, as are its homemade cheesecake and key lime pie. Warm summer weekends mean live entertainment and seating on the 40-foot deck. There's a deep-draft dock for diners arriving by boat. Waterman's gets very busy on the weekends, so be prepared to wait.

You can buy crabs here, of course, and have them served any number of imaginative ways. But slurp one of the thick homemade soups, or down the famous Carolina shrimp burger, to understand why this funky little eatery is so popular. The children's menu is a thoughtful extra. But go easy on the real food: Woody's ice-cream parlor, next door, includes seasonal favorite flavors such as apple, pumpkin, and Fourth of July (a celebration of red, white, and blue ice creams). Call ahead if you want traditional crabs. Woody's is quite hopping, so they occasionally run out.